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Yes the master clutch should be dry, and depending on the SN it might even be open. Mine is. I think I would do the following.

Remove the plug from the pony clutch, make sure the Diesel oil is at the proper level, start the Diesel then drain the pony oil. They donít hold much, then you could observe the volume of oil entering the pony crankcase. If thereís no oil dripping from the Clutch then youíd know you have a hole in the block of some sort.

Perhaps itís a block repair from the past thatís failed. Keep us posted whatever you find.